Eriosemaone C

Details

• Internal ID: ba873a2a-aadf-4592-97ce-eceed559994d
• Taxonomy: Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones
• IUPAC Name: (8S)-8-[3-(2,4-dihydroxyphenyl)-2,5,6-trihydroxyphenyl]-2,2-dimethyl-10-(3-methylbut-2-enyl)-7,8-dihydropyrano[3,2-g]chromen-6-one
• SMILES (Canonical): CC(=CCC1=C2C(=CC3=C1OC(CC3=O)C4=C(C(=CC(=C4O)O)C5=C(C=C(C=C5)O)O)O)C=CC(O2)(C)C)C
• SMILES (Isomeric): CC(=CCC1=C2C(=CC3=C1O[C@@H](CC3=O)C4=C(C(=CC(=C4O)O)C5=C(C=C(C=C5)O)O)O)C=CC(O2)(C)C)C
• InChI: InChI=1S/C31H30O8/c1-15(2)5-7-19-29-16(9-10-31(3,4)39-29)11-21-23(34)14-25(38-30(19)21)26-27(36)20(13-24(35)28(26)37)18-8-6-17(32)12-22(18)33/h5-6,8-13,25,32-33,35-37H,7,14H2,1-4H3/t25-/m0/s1
• InChI Key: XFFLLCTVQRLAND-VWLOTQADSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₃₀O₈
• Molecular Weight: 530.60 g/mol
• Exact Mass: 530.19406791 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 5.60
• Atomic LogP (AlogP): 6.28
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

• (S)-2',3',6'-Trihydroxy-8-prenyl-5'-(2,4-dihydroxyphenyl)-6'',6''-dimethylpyrano[2'',3'':7,6]flavanone
• (8S)-2,2-Dimethyl-10-(3-methylbut-2-en-1-yl)-8-(2,2',4,4',5-pentahydroxybiphenyl-3-yl)-7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-6-one
• CHEBI:73778
• LMPK12140004
• Q27144104
• (8S)-8-[3-(2,4-dihydroxyphenyl)-2,5,6-trihydroxy-phenyl]-2,2-dimethyl-10-(3-methylbut-2-enyl)-7,8-dihydropyrano[3,2-g]chromen-6-one
• (8S)-8-[3-(2,4-dihydroxyphenyl)-2,5,6-trihydroxyphenyl]-2,2-dimethyl-10-(3-methylbut-2-enyl)-7,8-dihydropyrano[3,2-g]chromen-6-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9529	95.29%
Caco-2	-	0.8174	81.74%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6804	68.04%
OATP2B1 inhibitior	-	0.7155	71.55%
OATP1B1 inhibitior	+	0.7515	75.15%
OATP1B3 inhibitior	+	0.9783	97.83%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9866	98.66%
P-glycoprotein inhibitior	+	0.7924	79.24%
P-glycoprotein substrate	+	0.6984	69.84%
CYP3A4 substrate	+	0.6733	67.33%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.7695	76.95%
CYP3A4 inhibition	-	0.7783	77.83%
CYP2C9 inhibition	+	0.6597	65.97%
CYP2C19 inhibition	+	0.6948	69.48%
CYP2D6 inhibition	-	0.8230	82.30%
CYP1A2 inhibition	-	0.7149	71.49%
CYP2C8 inhibition	+	0.7123	71.23%
CYP inhibitory promiscuity	+	0.6996	69.96%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6277	62.77%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.7868	78.68%
Skin irritation	-	0.7210	72.10%
Skin corrosion	-	0.9131	91.31%
Ames mutagenesis	+	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8958	89.58%
Micronuclear	-	0.5041	50.41%
Hepatotoxicity	-	0.5248	52.48%
skin sensitisation	-	0.7589	75.89%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.6957	69.57%
Acute Oral Toxicity (c)	III	0.5497	54.97%
Estrogen receptor binding	+	0.9172	91.72%
Androgen receptor binding	+	0.7966	79.66%
Thyroid receptor binding	+	0.5876	58.76%
Glucocorticoid receptor binding	+	0.8631	86.31%
Aromatase binding	+	0.6539	65.39%
PPAR gamma	+	0.7955	79.55%
Honey bee toxicity	-	0.7646	76.46%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	0.9824	98.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.80%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.26%	91.49%
CHEMBL2581	P07339	Cathepsin D	96.36%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.05%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.52%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.14%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.89%	89.00%
CHEMBL4208	P20618	Proteasome component C5	91.44%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.52%	94.45%
CHEMBL3038469	P24941	CDK2/Cyclin A	88.96%	91.38%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.73%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.64%	100.00%
CHEMBL3401	O75469	Pregnane X receptor	86.69%	94.73%
CHEMBL301	P24941	Cyclin-dependent kinase 2	86.64%	91.23%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.61%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	85.06%	94.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.05%	92.94%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	85.04%	90.71%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.29%	97.09%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.94%	85.00%
CHEMBL3922	P50579	Methionine aminopeptidase 2	81.86%	97.28%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	81.13%	96.38%
CHEMBL236	P41143	Delta opioid receptor	80.85%	99.35%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	80.71%	80.00%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	80.33%	95.64%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.29%	91.07%

Plants that contains it

• Eriosema tuberosum

Cross-Links

• PubChem: 10459657
• LOTUS: LTS0039596
• wikiData: Q27144104